Synthesis of Enantiopure Primary Amines by Stereoselective Ring Opening of Chiral Octahydro-1, 3-benzoxazines by Grignard and Organoaluminum Reagents

…, J Nieto, R Pedrosa, N Villamañán

Index: Andres, Celia; Nieto, Javier; Pedrosa, Rafael; Villamanan, Nieves Journal of Organic Chemistry, 1996 , vol. 61, # 12 p. 4130 - 4135

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Citation Number: 34

Abstract

Chiral 1, 3-perhydrobenzoxazines 1, 2, and 9-14, prepared by condensation of 8- (benzylamino) menthol with different aldehydes, react with alkylmagnesium bromides and trimethylaluminum leading to the open amino alcohols 3a-d, 4a-d, and 15-20 in excellent chemical yields and good to excellent diastereomeric excess. The sequential elimination of the menthol appendage by heating with P2O5 and the benzyl group by hydrogenolysis ...